N,N'-bis(2-hydroxyethyl)-1,7-dibromoperylene-3,4:9,10-tetracarboxylic diimide | 1314078-30-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: N,N'-bis(2-hydroxyethyl)-1,7-dibromoperylene-3,4:9,10-tetracarboxylic diimide
• CAS: 1314078-30-2
• 化学式: C₂₈H₁₆Br₂N₂O₆
• 分子量: 636.253
• InChiKey: SSTXOGVOTOJCSV-UHFFFAOYSA-N

物化性质

• 沸点：
  888.2±65.0 °C(Predicted)
• 密度：
  1.958±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  38.0
• 可旋转键数：
  4.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  115.22
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N,N'-bis(2-hydroxyethyl)-1,7-dibromoperylene-3,4:9,10-tetracarboxylic diimide 、 4,4'-双甲氧基三苯甲基氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 N-2-[(2-O-4,4-dimethoxytrytilethoxy)ethyl]-N'-2-(2-ethoxy)ethyl-1,7-dibromoperylene-3,4:9,10-tetracarboxylic diimide
  参考文献：
  名称：

  Synthesis of a Dibromoperylene Phosphoramidite Building Block and Its Incorporation at the 5′ End of a G-Quadruplex Forming Oligonucleotide: Spectroscopic Properties and Structural Studies of the Resulting Dibromoperylene Conjugate

  摘要：

  Previous studies indicate that some perylene bisimide derivatives can drive the assembly of DNA G-quadruplexes, thus suggesting the possible advantage in the adoption of perylene-conjugated G-rich oligonucleotides in biological and biotechnological applications. Nevertheless, the typical poor solubility of perylene bisimides strongly limits the number of suitable chemical strategies to prepare perylene-conjugated oligonucleotides. In order to overcome these difficulties, we employed the earlier described core twisted perylene derivatives possessing unique optical and electronic properties, besides good solubility in common solvents. As a first result, the large-scale synthesis of a new dibromoperylene derivative (PEOEBr) phosphoramidite building block is herein reported. Furthermore, the structural behavior of the conjugated PEOEBr-GGGTTAGGG (HTRp2) human telomeric repeat was investigated by using CD, UV, fluorescence, and gel electrophoresis techniques in desalted water and in K+- and Na+-containing buffers. We observed that the peculiar property of PEOEBr moieties to form dimers instead of extended aggregates drives the HTRp2 strands toward dimerization and mainly promotes the formation of quadruplex species having both the 5'-ends located at the same side of the structures. However, the counterions present in solutions (K+ or Na+) as well as the strand concentration, also contribute to influence the topology and the stoichiometry of formed structures. Furthermore, unlike the unmodified sequence GGGTTAGGG (HTR2), HTRp2 strands quickly associate into G-quadruplexes even in desalted water, as assessed by CD experiments.

  DOI：

  10.1021/bc100526q
• 作为产物：
  描述：

  在 甲醇 、 氨 作用下， 以 水 为溶剂， 反应 2.0h， 以100%的产率得到N,N'-bis(2-hydroxyethyl)-1,7-dibromoperylene-3,4:9,10-tetracarboxylic diimide
  参考文献：
  名称：

  Synthesis of a Dibromoperylene Phosphoramidite Building Block and Its Incorporation at the 5′ End of a G-Quadruplex Forming Oligonucleotide: Spectroscopic Properties and Structural Studies of the Resulting Dibromoperylene Conjugate

  摘要：

  Previous studies indicate that some perylene bisimide derivatives can drive the assembly of DNA G-quadruplexes, thus suggesting the possible advantage in the adoption of perylene-conjugated G-rich oligonucleotides in biological and biotechnological applications. Nevertheless, the typical poor solubility of perylene bisimides strongly limits the number of suitable chemical strategies to prepare perylene-conjugated oligonucleotides. In order to overcome these difficulties, we employed the earlier described core twisted perylene derivatives possessing unique optical and electronic properties, besides good solubility in common solvents. As a first result, the large-scale synthesis of a new dibromoperylene derivative (PEOEBr) phosphoramidite building block is herein reported. Furthermore, the structural behavior of the conjugated PEOEBr-GGGTTAGGG (HTRp2) human telomeric repeat was investigated by using CD, UV, fluorescence, and gel electrophoresis techniques in desalted water and in K+- and Na+-containing buffers. We observed that the peculiar property of PEOEBr moieties to form dimers instead of extended aggregates drives the HTRp2 strands toward dimerization and mainly promotes the formation of quadruplex species having both the 5'-ends located at the same side of the structures. However, the counterions present in solutions (K+ or Na+) as well as the strand concentration, also contribute to influence the topology and the stoichiometry of formed structures. Furthermore, unlike the unmodified sequence GGGTTAGGG (HTR2), HTRp2 strands quickly associate into G-quadruplexes even in desalted water, as assessed by CD experiments.

  DOI：

  10.1021/bc100526q

文献信息

• Precision Cancer Theranostic Platform by In Situ Polymerization in Perylene Diimide-Hybridized Hollow Mesoporous Organosilica Nanoparticles
  作者：Zhen Yang、Wenpei Fan、Jianhua Zou、Wei Tang、Ling Li、Liangcan He、Zheyu Shen、Zhantong Wang、Orit Jacobson、Maria A. Aronova、Pengfei Rong、Jibin Song、Wei Wang、Xiaoyuan Chen

  DOI：10.1021/jacs.9b06086

  日期：2019.9.18

  photothermal/chemo therapy, photothermal/photodynamic therapy, and photodynamic/chemo therapy, which are expected to provide a paradigm of modern precision medicine. In this regard, various phototheranostic drug delivery systems with excellent photonic performance, controlled drug delivery/release, and precise photo-imaging guidance have been developed. In this study, we reported a special "in situ framework growth"

  光疗是指先进的光子学介导的癌症治疗方法，包括成像引导的光热/化学疗法、光热/光动力疗法和光动力/化学疗法，有望提供现代精准医学的范例。在这方面，已经开发了具有优异光子性能、受控药物递送/释放和精确光成像引导的各种光疗药物递送系统。在这项研究中，我们报道了一种特殊的“原位框架生长”方法，通过在小尺寸中空介孔有机硅 (HMO) 框架内巧妙地杂化苝二亚胺 (PDI) 来合成新型光疗中空介孔纳米粒子。PDI 和 HMO 的结合赋予了光疗二氧化硅纳米粒子 (HMPDINs) 以大幅放大的荧光和光声信号，可用于增强荧光和光声成像。有机硅壳可以与同位素 64Cu 化学螯合，用于正电子发射断层扫描成像。此外，在 HMPDINs 的中空结构中引入了原位聚合物生长，以在 HMPDINs 的空腔中产生热敏聚合物 (TP)，以增加负载能力并防止疏水性药物 SN38 意外泄漏。此外，框架杂交的 PDI 在近红外激光照射下产生热量，触发